(Z)-(2S,3S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2-methyl-non-6-en-1-one

Base Information

• Chemical Name: (Z)-(2S,3S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2-methyl-non-6-en-1-one
• CAS No.: 502927-14-2
• Molecular Formula: C₃₆H₅₁NO₅SSi
• Molecular Weight: 637.956

Synonyms:(Z)-(2S,3S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2-methyl-non-6-en-1-one

Chemical Property of (Z)-(2S,3S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2-methyl-non-6-en-1-one

Chemical Property:

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Technology Process of (Z)-(2S,3S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2-methyl-non-6-en-1-one

There total 1 articles about (Z)-(2S,3S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2-methyl-non-6-en-1-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

N-propionyl-(2R)-bornane-(10,2)-sultam (125664-95-1) + (4Z,6S)-<(tert-butyldiphenylsilyl)oxy>-4-heptenal (175084-42-1) → (Z)-(2S,3S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-hydroxy-2-methyl-non-6-en-1-one (502927-14-2)

Guidance literature:

N-propionyl-(2R)-bornane-(10,2)-sultam; With N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In hexane; dichloromethane; at -5 ℃; for 0.5h;

(4Z,6S)-<(tert-butyldiphenylsilyl)oxy>-4-heptenal; In hexane; dichloromethane; at -78 ℃; for 1h; Further stages.;

DOI:10.1039/b206656d

Reference yield:

(Z)-(2S,3S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-hydroxy-2-methyl-non-6-en-1-one (502927-14-2) → (S)-2-{(2S,5R)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-propan-1-one (502927-16-4)

Guidance literature:

(Z)-(2S,3S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2-methyl-non-6-en-1-one; With mercury(II) diacetate; In dichloromethane; at 20 ℃; for 24h;

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 20 ℃; for 2h; Further stages.;

DOI:10.1039/b206656d

Reference yield:

(Z)-(2S,3S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-hydroxy-2-methyl-non-6-en-1-one (502927-14-2) → methyl 8-benzoyl-(2S,3S,6R,8R)-nonactate (173396-36-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Hg(OAc)2 / CH₂Cl₂ / 24 h / 20 °C

1.2: 1.28 g / Bu₃SnH; AIBN / toluene / 2 h / 20 °C

2.1: aq. LiOH; H₂O₂ / tetrahydrofuran / 7 h / 20 °C

3.1: diethyl ether / 1 h / 0 °C

4.1: 79 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

5.1: 82 percent / PPh₃; DEAD / tetrahydrofuran / 18 h / 20 °C

With lithium hydroxide; mercury(II) diacetate; tetrabutyl ammonium fluoride; dihydrogen peroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; 5.1: Mitsunobu reaction;

DOI:10.1039/b206656d

upstream raw materials:

N-propionyl-(2R)-bornane-(10,2)-sultam

(4Z,6S)-<(tert-butyldiphenylsilyl)oxy>-4-heptenal

Downstream raw materials:

(S)-2-{(2S,5R)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-propan-1-one

methyl 8-benzoyl-(2S,3S,6R,8R)-nonactate

(+)-methyl 8-epi-8-O-(tert-butyldiphenylsilyl)nonactate

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